7694-45-3

• 常用中文名：紫苏酸
• 常用英文名：(S)-(-)-PERILLIC ACID
• CAS号：7694-45-3
• 分子式：C₁₀H₁₄O₂
• 分子量：166.21700
• 相关类别： 信号通路 抗感染 HSV
• 发布时间：2018-06-29 11:33:04
• 更新时间：2024-01-05 00:41:00
• 紫苏酸是紫苏醇(HY-N7000)的代谢产物。紫苏酸诱导肺癌细胞周期阻滞和凋亡。Perillic acid显示抗HSV-1和免疫调节活性[1][2][3]。

名称

• 中文名: 紫苏酸
• 英文名: perillic acid
• 英文别名: (S)-(-)-perillyc acid; 4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid; (4S)-[2-propenyl]-1-cyclohexene-1-carboxylic acid; 4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid; MFCD02114258; 4-Isopropenylcyclohex-1-enecarboxylic acid; (S)-(-)-perillic cid; (S)-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylic acid; 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid; (S)-(-)-4-isopropenylcyclohexene-1-carboxylic acid; Perillic acid; EINECS 231-709-5; 4-Isopropenyl-1-cyclohexene-1-carboxylic acid

物化性质

• 密度: 1.068 g/cm3
• 沸点: 284.9ºC at 760 mmHg
• 熔点: 129-131 °C(lit.)
• 分子式: C₁₀H₁₄O₂
• 分子量: 166.21700
• 闪点: 134ºC
• 精确质量: 166.09900
• PSA: 37.30000
• LogP: 2.37360
• 外观性状: 白色固体
• 折射率: 1.513
• 储存条件:

  2-8℃

• 分子结构:

  1、 摩尔折射率：46.75

  2、 摩尔体积（m³/mol）：155.5

  3、 等张比容（90.2K）：390.4

  4、 表面张力（dyne/cm）：39.7

  5、 极化率（10 ^-24cm ³）：18.53

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.7

  2.氢键供体数量:1

  3.氢键受体数量:2

  4.可旋转化学键数量:2

  5.互变异构体数量:无

  6.拓扑分子极性表面积37.3

  7.重原子数量:12

  8.表面电荷:0

  9.复杂度:238

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:1

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：未确定

  2. 密度（g/mL 25ºC）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：129-135

  5. 沸点（ºC，常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率（n20/D）：未确定

  8. 闪点（ºC，）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值（25℃）：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性(mg/mL)：未确定

生物活性

• 描述: 紫苏酸是紫苏醇(HY-N7000)的代谢产物。紫苏酸诱导肺癌细胞周期阻滞和凋亡。Perillic acid显示抗HSV-1和免疫调节活性[1][2][3]。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  研究领域 >> 癌症
  信号通路 >> 抗感染 >> HSV
  研究领域 >> 感染
  研究领域 >> 炎症/免疫
• 靶点:

  HSV-1

• 体外研究: Perillic酸(1-5 mM；24小时)以剂量依赖的方式降低 第549页细胞的存活率[1]。 Perillic acid(1 mM；24小时)诱导 第549页细胞 S期阻滞,诱导 人520细胞 G2/米期阻滞[1]。 Perillic酸(2mM；24小时)诱导 第549页和 人520细胞凋亡[1]。 Perillic acid(0-50μM；24小时)显示出主要针对 17syn+HSV-1的抗病毒活性 (EC50 KOS:2.84μM；17syn+：1.08μM)[2]细胞细胞毒性试验[1]细胞系：A549细胞浓度：1、2、3、4和5 mM培养时间：24小时结果：导致存活率以剂量依赖性的方式降低,IC50为3.6 mM。细胞周期分析[1]细胞系A549和H520细胞浓度：1mM培养时间：24小时。结果：在A549细胞中诱导S期阻滞,在H520细胞中诱导G2/M期阻滞。细胞凋亡分析[1]细胞系：A549和H520细胞浓度：2mM培养时间：24小时结果：与对照组(12%)相比,A549细胞的凋亡增加到27%,H520细胞的凋亡减少到18%。Western Blot分析[1]细胞系：H520细胞浓度：0.5 mM培养时间：24小时结果：Bax表达增加,蛋白酶原-3水平降低。
• 体内研究: Perillic acid(50μM/kg；腹腔注射；每天5天)显示小鼠免疫调节活性[3]。 动物模型：Balb/c小鼠[3]剂量：50μM/kg给药：腹膜内注射,每天5天结果：白细胞总数(WBC)增加。与正常动物相比,总抗体产生量、脾脏中的抗体产生细胞、骨髓细胞和α-酯酶阳性细胞显著增加。
• 参考文献:

  [1]. Yeruva L, et al. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer Lett. 2007 Nov 18;257(2):216-26.

  [2]. Mello CP, et al. Perillyl alcohol and perillic acid exert efficient action upon HSV-1 maturation and release of infective virus. Antivir Ther. 2020;25(1):1-11.

  [3]. Raphael TJ, et al. Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid. Immunopharmacol Immunotoxicol. 2003 May;25(2):285-94.

MSDS

Name: L-(-)-Perillic Acid 95% Material Safety Data Sheet Synonym: None CAS: 7694-45-3 Section 1 - Chemical Product MSDS Name:L-(-)-Perillic Acid 95% Material Safety Data Sheet Synonym:None Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 7694-45-3 L-(-)-Perillic Acid 95 231-709-5 Hazard Symbols: XI Risk Phrases: 36/37/38 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: Causes eye irritation. The toxicological properties of this material have not been fully investigated. Skin: Causes skin irritation. The toxicological properties of this material have not been fully investigated. Ingestion: Causes gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Inhalation: Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Chronic: No information found. Section 4 - FIRST AID MEASURES Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Store in a cool, dry place. Keep container closed when not in use. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels. Exposure Limits CAS# 7694-45-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to minimize contact with skin. Respirators: Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: cream Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 129.00 - 131.00 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: N/A Explosion Limits, upper: N/A Decomposition Temperature: Solubility in water: Specific Gravity/Density: Molecular Formula: C10H14O2 Molecular Weight: 166.22 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Irritating and toxic fumes and gases. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 7694-45-3: GW4564565 LD50/LC50: Not available. Carcinogenicity: L-(-)-Perillic Acid - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: XI Risk Phrases: R 36/37/38 Irritating to eyes, respiratory system and skin. Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 7694-45-3: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 7694-45-3 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 7694-45-3 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 急性毒性：LD50：4000mg/Kg（大鼠经口）；4720mg/Kg（兔经皮）。 LC50：9400mg/m3，2小时（小鼠吸入）

安全

• 危害码 (欧洲): Xi: Irritant;
• 风险声明 (欧洲): 36/37/38
• 安全声明 (欧洲): S26-S36
• WGK德国: 3
• 海关编码: 2916209090

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海关

海关编码	2916209090
中文概述	2916209090 其他（环烷、环烯、环萜烯）一元羧酸（包括酸酐、酰卤化物，过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0% 退税率:9.0% 监管条件:AB(入境货物通关单,出境货物通关单) 最惠国关税:6.5% 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 丙烯酸、丙烯酸盐或酯应报明包装
监管条件	A.入境货物通关单 B.出境货物通关单
检验检疫	R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验
Summary	2916209090 other cyclanic, cyclenic or cyclotherpenic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%